Pyrrolidine → 2,6-Dimethyl-3-(pyrrolidin-1-yl)aniline

HRID 1182264Notes

Reaction equation

HRID 1182264 reaction equation
Br[C:2]1[C:3]([CH3:10])=[C:4]([NH2:9])[C:5]([CH3:8])=[CH:6][CH:7]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[CH3:10][C:3]1[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=[C:5]([CH3:8])[C:4]=1[NH2:9]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 12792330HCID 12792330, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 204950152,6-Dimethyl-3-(pyrrolidin-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-bromo-2,6-dimethylphenylamine(0.27 g, 1.35 mmol) dissolved in toluene (5.4 mL) and pyrrolidine (0.56 mL, 6.8 mmol) was added sodium t-butoxide (0.39 g, 4.0 mmol). The suspension was deoxygenated for approximately 10 minutes by passing a stream of nitrogen through the solvent. Solid tris(dibenzilideneacetone)dipalladium(0) (10 mg) and rac-2,2′Bis(diphenylphosphino)-1,1′binaphthyl (25 mg) were combined and added in one portion. Nitrogen bubbling continued for an additional 2 minutes before heat was applied (100° C. overnight). The reaction mixture was cooled to room temperature and diluted with ethyl acetate and HClaq. (2N). The aqueous layer was adjusted basic with sodium bicarbonate solution and re-extracted with ethyl acetate. The organic layer was dried over sodium sulfate, decanted and concentrated under reduced pressure to give to give the desired 2,6-dimethyl-3-pyrrolidin-1-ylphenylamine as an amber oil.

Workup

  1. customThe suspension was deoxygenated for approximately 10 minutes
  2. additionadded in one portion
  3. temperaturebefore heat
  4. custom(100° C. overnight)
  5. additiondiluted with ethyl acetate and HClaq
  6. extractionre-extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. customdecanted
  9. concentrationconcentrated under reduced pressure
  10. customto give

Sources & evidence

ORD record
ord-0776e09ac4164210b6d19aeaa0952383
Source dataset
uspto-grants-2007_10
Patent number
US07288538B2

Reaction notes

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